Perfume systems

ABSTRACT

The present application relates to perfume delivery systems and consumer products comprising perfume delivery systems and or perfume raw materials, as well as processes for making and using such perfume delivery systems and consumer products.

This is a continuation of U.S. patent application Ser. No. 14/334,692,filed Jan. 18, 2013, now U.S. Patent No. 9,441,185.

FIELD OF INVENTION

The present application relates to perfume delivery systems and consumerproducts comprising such perfume delivery systems and/or perfume rawmaterials as defined herein, as well as processes for making and usingsuch perfume delivery systems and consumer products.

BACKGROUND OF THE INVENTION

Consumer products may comprise one or more perfumes and/or perfumedelivery systems that can mask an undesirable odor and/or provide adesired scent to a product and/or a situs that is contacted with such aproduct. While current perfumes and perfume delivery systems providedesirable fragrances, consumers continue to seek products that havescents that may be longer lasting and that are tailored to theirindividual desires (see for example USPA 2007/0275866 A1 and USPA2008/0305977 A1)—unfortunately the pool of perfume raw materials andperfume delivery systems that is available is still too limited tocompletely meet the perfume community's needs. Thus, perfumers need anever larger pool of perfume raw materials and perfume delivery systems.

Applicants believe that the perfume raw materials and perfumes,including the delivery systems, disclosed herein expand the perfumecommunity's options, as such perfume raw materials can providevariations on character and such perfumes can provide desired odorprofiles in consumer products. In certain aspects, such perfume deliverysystems comprising such perfume raw materials may provide variations oncharacter and/or odor profiles that are better than expected as measuredby parameters such as headspace analysis (employed to determine perfumedelivery system perfume leakage and/or perfume delivery efficiency), Clog P, boiling point and/or odor detection threshold.

SUMMARY OF THE INVENTION

The present application relates to perfume delivery systems and consumerproducts comprising such perfume delivery systems and/or perfume rawmaterials, as well as processes for making and using such perfumedelivery systems and consumer products.

DETAILED DESCRIPTION OF THE INVENTION

Definitions

As used herein “consumer product” means baby care, beauty care, fabric &home care, family care, feminine care, health care, snack and/orbeverage products or devices generally intended to be used or consumedin the form in which it is sold. Such products include but are notlimited to diapers, bibs, wipes; products for and/or methods relating totreating hair (human, dog, and/or cat), including, bleaching, coloring,dyeing, conditioning, shampooing, styling; deodorants andantiperspirants; personal cleansing; cosmetics; skin care includingapplication of creams, lotions, and other topically applied products forconsumer use including fine fragrances; and shaving products, productsfor and/or methods relating to treating fabrics, hard surfaces and anyother surfaces in the area of fabric and home care, including: air careincluding air fresheners and scent delivery systems, car care,dishwashing, fabric conditioning (including softening and/orfreshening), laundry detergency, laundry and rinse additive and/or care,hard surface cleaning and/or treatment including floor and toilet bowlcleaners, and other cleaning for consumer or institutional use; productsand/or methods relating to bath tissue, facial tissue, paperhandkerchiefs, and/or paper towels; tampons, feminine napkins; productsand/or methods relating to oral care including toothpastes, tooth gels,tooth rinses, denture adhesives, tooth whitening; over-the-counterhealth care including cough and cold remedies, pain relievers, RXpharmaceuticals, pet health and nutrition; processed food productsintended primarily for consumption between customary meals or as a mealaccompaniment (non-limiting examples include potato chips, tortillachips, popcorn, pretzels, corn chips, cereal bars, vegetable chips orcrisps, snack mixes, party mixes, multigrain chips, snack crackers,cheese snacks, pork rinds, corn snacks, pellet snacks, extruded snacksand bagel chips); and coffee.

As used herein, the term “cleaning and/or treatment composition” is asubset of consumer products that includes, unless otherwise indicated,beauty care, fabric & home care products. Such products include, but arenot limited to, products for treating hair (human, dog, and/or cat),including, bleaching, coloring, dyeing, conditioning, shampooing,styling; deodorants and antiperspirants; personal cleansing; cosmetics;skin care including application of creams, lotions, and other topicallyapplied products for consumer use including fine fragrances; and shavingproducts, products for treating fabrics, hard surfaces and any othersurfaces in the area of fabric and home care, including: air careincluding air fresheners and scent delivery systems, car care,dishwashing, fabric conditioning (including softening and/orfreshening), laundry detergency, laundry and rinse additive and/or care,hard surface cleaning and/or treatment including floor and toilet bowlcleaners, granular or powder-form all-purpose or “heavy-duty” washingagents, especially cleaning detergents; liquid, gel or paste-formall-purpose washing agents, especially the so-called heavy-duty liquidtypes; liquid fine-fabric detergents; hand dishwashing agents or lightduty dishwashing agents, especially those of the high-foaming type;machine dishwashing agents, including the various tablet, granular,liquid and rinse-aid types for household and institutional use; liquidcleaning and disinfecting agents, including antibacterial hand-washtypes, cleaning bars, mouthwashes, denture cleaners, dentifrice, car orcarpet shampoos, bathroom cleaners including toilet bowl cleaners; hairshampoos and hair-rinses; shower gels, fine fragrances and foam bathsand metal cleaners; as well as cleaning auxiliaries such as bleachadditives and “stain-stick” or pre-treat types, substrate-laden productssuch as dryer added sheets, dry and wetted wipes and pads, nonwovensubstrates, and sponges; as well as sprays and mists all for consumeror/and institutional use; and/or methods relating to oral care includingtoothpastes, tooth gels, tooth rinses, denture adhesives, toothwhitening.

As used herein, the term “fabric and/or hard surface cleaning and/ortreatment composition” is a subset of cleaning and treatmentcompositions that includes, unless otherwise indicated, granular orpowder-form all-purpose or “heavy-duty” washing agents, especiallycleaning detergents; liquid, gel or paste-form all-purpose washingagents, especially the so-called heavy-duty liquid types; liquidfine-fabric detergents; hand dishwashing agents or light dutydishwashing agents, especially those of the high-foaming type; machinedishwashing agents, including the various tablet, granular, liquid andrinse-aid types for household and institutional use; liquid cleaning anddisinfecting agents, including antibacterial hand-wash types, cleaningbars, car or carpet shampoos, bathroom cleaners including toilet bowlcleaners; and metal cleaners, fabric conditioning products includingsoftening and/or freshening that may be in liquid, solid and/or dryersheet form; as well as cleaning auxiliaries such as bleach additives and“stain-stick” or pre-treat types, substrate-laden products such as dryeradded sheets, dry and wetted wipes and pads, nonwoven substrates, andsponges; as well as sprays and mists. All of such products which wereapplicable may be in standard, concentrated or even highly concentratedform even to the extent that such products may in certain aspect benon-aqueous.

As used herein, articles such as “a” and “an” when used in a claim, areunderstood to mean one or more of what is claimed or described.

As used herein, the terms “include”, “includes” and “including” aremeant to be non-limiting.

As used herein, the term “solid” includes granular, powder, bar andtablet product forms.

As used herein, the term “fluid” includes liquid, gel, paste and gasproduct forms.

As used herein, the term “situs” includes paper products, fabrics,garments, hard surfaces, hair and skin.

Unless otherwise noted, all component or composition levels are inreference to the active portion of that component or composition, andare exclusive of impurities, for example, residual solvents orby-products, which may be present in commercially available sources ofsuch components or compositions.

All percentages and ratios are calculated by weight unless otherwiseindicated. All percentages and ratios are calculated based on the totalcomposition unless otherwise indicated.

It should be understood that every maximum numerical limitation giventhroughout this specification includes every lower numerical limitation,as if such lower numerical limitations were expressly written herein.Every minimum numerical limitation given throughout this specificationwill include every higher numerical limitation, as if such highernumerical limitations were expressly written herein. Every numericalrange given throughout this specification will include every narrowernumerical range that falls within such broader numerical range, as ifsuch narrower numerical ranges were all expressly written herein.

Perfume Raw Materials (Herein after “PRMs”)

Suitable PRMs for employment in perfume delivery systems and/or consumerproducts as detailed herein include the PRMs listed in Table 1 below andstereoisomers thereof.

TABLE 1 Chemical Structure IUPAC Names Character description  1

4-(2,4-dimethyl-cyclohex- 3-enylidene)-butan-2-one strong woody andspicy characters  2

4-isopropyl-1,5-dimethyl-2- oxa-bicyclo[2.2.2]octane herbal, camphor,woody, minty, and patchouli aspects  3

4-(1,2-dimethyl-propyl)-1- methyl-2-oxa- bicyclo[2.2.2]octane anisic,green, powdery, and fruity notes  4

2-(3-methyl-butyl)-3-vinyl- cyclopentanone lactonic, peach, buttery,floral, fruity, marigold, green, herbaceous, and minty characters  5

2,5,5-trimethyl-2-propyl- [1,3]dioxane fruity and anise characters  6

1,2,4-trimethyl- bicyclo[2.2.1]heptane-2- carboxylic acid methyl esterwoody, pine, camphor, herbal, and earthy characters  7

8-ethoxy-2,6-dimethyl- nona-2,6-diene grapefruit, citrus, fresh,lemonile, lemonalva, and metallic characters  8

2,2,3a,7-tetramethyl- octahydro-benzofuran herbal, sweet, camphor,woody, fresh, and green notes  9

3a-isopropyl-2,6-dimethyl- octahydro-benzofuran cedar wood, green,spice, flora, eucalyptus, and slight piney notes 10

4- cyclopropylmethoxymethyl- 5-methyl-cyclohexene strong fruity andgreen characters 11

cyclopropanecarboxylic acid 1-methyl-hexyl ester strong fruity, herbal,seaweed, chamomile, and ambrette seed characters 12

3-isopropenyl-6-methyl-2- propenyl-tetrahydro-pyran strong woody, fresh,cinnamon, and spicy characters 13

acetic acid 3-isopropyl-1,2- dimethyl-cyclopentyl ester strong woody,fresh, cinnamon, and spicy characters 14

1-(2,4,6-trimethyl- cyclohex-3-enyl)-propan-1- one animalic, civet,chrysanthemum leaves, and honey notes 16

2-(hex-3-enyl)-5-methyl- tetrahydro-furan strong floral and vegetablecharacters 17

3-sec-Butyl-1,5-dimethyl-2- oxa-bicyclo[2.2.2]octane sweet, warm, black-pepper, herbal 18

1-(6-Isopropyl-2-methyl- cyclohex-3-enyl)-ethanone damascone-like,minty, rosey 19

1-(6-Isopropyl-4-methyl- cyclohex-3-enyl)-ethanone floral (rose), muskaspects, must spicy, slightly green 20

4-(3-Methoxy-1-methyl- propyl)-1-methyl- cyclohexene black licorice,green, floral 21

3-(1,1-Dimethoxy-ethyl)- 1,1-dimethyl-cyclohexane candy, herbaceous,fruity, minty 22

2,4-Dimethyl-2-(4-methyl- pent-3-nyl)-[1,3]dioxolane floral, green,sweet, rose

The PRMs disclosed in Table 1 above (a.k.a., molecules—as referred to inthe Examples section) may provide one or more of the following benefitsat levels that Applicants believe are unexpected in view of PRMs ingeneral: neat product odor; wet fabric odor when applied to a fabric;dry fabric odor when applied to a fabric; reduced leakage from anencapsulate, including an encapsulate such as a perfume microcapsule;increased head space versus neat oil in certain perfume deliverytechnologies; odor when used in a matrix perfume delivery that isapplied to a package; neat product odor when applied to a cleaningand/or treatment composition; fine fragrance composition odor when usedin a fine fragrance; dry hair odor when a composition comprising such aPRM is applied to hair; PRM bloom from a solution comprising such a PRM;and new PRM character when applied to a situs. Confirmation of suchbenefits can be obtained by applying standard test methodologiesdetailed herein. The PRMs and stereoisomers of such PRMs disclosed inTable 1 above can be made in accordance with the teachings detailed inthe present specification.

In one aspect, the PRMs disclosed in Table 1 and stereoisomers thereofare suitable for use, as defined by the present specification, inconsumer products at levels, based on total consumer product weight, offrom about 0.0001% to about 25%, from about 0.0005% to about 10%, fromabout 0.001% to about 5%, from about 0.005% to about 2.5%, or even from0.01% to about 1%. Such PRMs and stereoisomers thereof may be used invarious combinations in the aforementioned consumer products. In oneaspect, a consumer product may comprise one or more PRMs selected fromTable 1 Nos. 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17,18, 19, 20, 21, 22 and stereoisomers thereof.

In another aspect, the PRMs disclosed in Table 1 and stereoisomersthereof are suitable for use, as defined by the present specification,in cleaning and/or treatment compositions at levels, based on totalcleaning and treatment products weight of from about 0.0001% to about25%, from about 0.0005% to about 10%, from about 0.001% to about 5%,from about 0.005% to about 2.5%, or even from 0.01% to about 1%. SuchPRMs and stereoisomers thereof may be used in various combinations inthe aforementioned cleaning and/treatment compositions. In one aspect, acleaning and/or treatment composition may comprise one or more PRMsselected from Table 1 Nos. 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13,14, 15, 16, 17, 18, 19, 20, 21, 22 and stereoisomers thereof.

In another aspect, the PRMs disclosed in Table 1 and stereoisomersthereof are suitable for use, as defined by the present specification,in fabric and/or hard surface cleaning and/or treatment compositions atlevels, based on total fabric and/or hard surface cleaning and/ortreatment composition weight of from about 0.00001% to about 25%, from0.00005% to about 10%, from 0.0001% to about 5%, from 0.0005% to about1.0%, or even from 0.001% to about 0.5%. Such PRMs and stereoisomersthereof may be used in various combinations in the aforementioned fabricand/or hard surface cleaning and/or treatment compositions. In oneaspect, a fabric and/or hard surface cleaning and/or treatmentcomposition may comprise one or more PRMs selected from Table 1 Nos. 1,2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21,22 and stereoisomers thereof.

In another aspect, a detergent that may comprise the same level of thePRMs as disclosed for the aforementioned fabric and hard surfacecleaning and/or treatment compositions is disclosed. In one aspect, adetergent may comprise one or more PRMs selected from Table 1 Nos. 1, 2,3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22and stereoisomers thereof.

In another aspect, the PRMs disclosed in Table 1 and stereoisomersthereof are suitable for use in highly compacted consumer products,including highly compacted fabric and hard surface cleaning and/ortreatment compositions. For example, the PRMs disclosed in Table 1 andstereoisomers thereof may be employed in solid or fluid highly compacteddetergents at levels of from about 0.00001% to about 25%, from 0.00005%to about 10%, from 0.0001% to about 5%, from 0.0005% to about 1.0%, oreven from 0.001% to about 0.5%, based on total composition weight. SuchPRMs and stereoisomers thereof may be used in various combinations inthe aforementioned highly compacted detergent compositions. Such highlycompact detergents typically comprise a higher than normal percentage ofactive ingredients. In one aspect, a highly compacted detergent maycomprise one or more PRMs selected from Table 1 Nos. 1-94 andstereoisomers thereof. More specifically, a highly compacted detergentmay comprise one or more PRMs selected from Table 1 Nos. 1, 2, 3, 4, 5,6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22 andstereoisomers thereof.

Perfume Delivery Systems

The perfume raw materials and perfume compositions disclosed herein mayfurther be incorporated into a perfume delivery system. Suitable perfumedelivery systems, methods of making perfume delivery systems and theuses of perfume delivery systems are disclosed in USPA 2007/0275866 A1.Such perfume delivery systems include:

-   I. Polymer Assisted Delivery (PAD): This perfume delivery technology    uses polymeric materials to deliver perfume materials. Examples of    PAD include employment of classical coacervation, water soluble or    partly soluble to insoluble charged or neutral polymers, liquid    crystals, hot melts, hydrogels, perfumed plastics, microcapsules,    nano- and micro-latexes, polymeric film formers, and polymeric    absorbents, etc. Further, PAD includes, but is not limited to:

a.) Matrix Systems: The perfume is dissolved or dispersed in a polymermatrix or particle. Perfume materials may be 1) dispersed into thepolymer prior to formulating into the product or 2) added separatelyfrom the polymer during or after formulation of the product. Suitableorganic latex particles include a wide range of materials including, butnot limited to, polyacetal, polyacrylate, polyamide, polybutadiene,polychloroprene, polyethylene, polycyclohexylene polycarbonate,polyhydroxyalkanoate, polyketone, polyester, polyetherimide,polyethersulfone, polyethylenechlorinates, polyimide, polyisoprene,polylactic acid, polyphenylene, polyphenylene, polypropylene,polystyrene, polysulfone, polyvinyl acetate, polyvinyl chloride, as wellas polymers or copolymers based on amine, acrylonitrile-butadiene,cellulose acetate, ethylene-vinyl acetate, ethylene vinyl alcohol,styrene-butadiene, vinyl acetate-ethylene, and mixtures thereof. Allsuch matrix systems may include, for example, polysaccharides andnanolatexes that may be combined with other perfume deliverytechnologies, including other PAD systems such as PAD reservoir systemsin the form of a perfume microcapsule (PMC). Silicone-assisted delivery(SAD) may also be used. Examples of silicones includepolydimethylsiloxane and polyalkyldimethylsiloxanes. Other examplesinclude those with amine functionality, which may be used to providebenefits associated with amine-assisted delivery (AAD) and/orpolymer-assisted delivery (PAD) and/or amine-reaction products (ARP).

b.) Reservoir Systems: Reservoir systems are also known as core-shellsystems (e.g., perfume microcapsules). In such a system, the benefitagent is surrounded by a benefit agent release controlling membrane,which may serve as a protective shell. Suitable shell materials includereaction products of one or more amines with one or more aldehydes, suchas urea cross-linked with formaldehyde or gluteraldehyde, melaminecross-linked with formaldehyde, gelatin-polyphosphate coacervatesoptionally cross-linked with gluteraldehyde, gelatin-gum arabiccoacervates, cross-linked silicone fluids, polyamine reacted withpolyisocyanates, polyamines reacted with epoxides, polyvinyl alcoholcross linked with gluteraldehyde, polydivinyl chloride, polyesters,polyamides, polyacrylates and mixtures thereof. In one aspect, saidpolyacrylate based materials may comprise polyacrylate formed frommethylmethacrylate/dimethylaminomethyl methacrylate, polyacrylate formedfrom amine acrylate and/or methacrylate and strong acid, polyacrylateformed from carboxylic acid acrylate and/or methacrylate monomer andstrong base, polyacrylate formed from an amine acrylate and/ormethacrylate monomer and a carboxylic acid acrylate and/or carboxylicacid methacrylate monomer, and mixtures thereof.

Suitable core materials include perfume compositions, perfume rawmaterials, silicone oils, waxes, hydrocarbons, higher fatty acids,essential oils, lipids, skin coolants, vitamins, sunscreens,antioxidants, glycerine, catalysts, bleach particles, silicon dioxideparticles, malodor reducing agents, odor-controlling materials,chelating agents, antistatic agents, softening agents, insect and mothrepelling agents, colorants, antioxidants, chelants, bodying agents,drape and form control agents, smoothness agents, wrinkle controlagents, sanitization agents, disinfecting agents, germ control agents,mold control agents, mildew control agents, antiviral agents, dryingagents, stain resistance agents, soil release agents, fabric refreshingagents and freshness extending agents, chlorine bleach odor controlagents, dye fixatives, dye transfer inhibitors, color maintenanceagents, optical brighteners, color restoration/rejuvenation agents,anti-fading agents, whiteness enhancers, anti-abrasion agents, wearresistance agents, fabric integrity agents, anti-wear agents,anti-pilling agents, defoamers and anti-foaming agents, UV protectionagents for fabrics and skin, sun fade inhibitors, anti-allergenicagents, enzymes, water proofing agents, fabric comfort agents, shrinkageresistance agents, stretch resistance agents, stretch recovery agents,skin care agents, glycerin, and natural actives such as aloe vera,vitamin E, shea butter, cocoa butter, and the like, brighteners,antibacterial actives, antiperspirant actives, cationic polymers, dyesand mixtures thereof. Suitable perfume compositions may compriseenduring perfumes, such as perfume raw materials that have a c Log Pgreater than about 2.5 and a boiling point greater than about 250° C.Further, suitable perfume compositions may comprise blooming perfumesthat comprise perfume raw materials that have a c Log P of greater thanabout 3 and a boiling point of less than about 260° C.

Suitable core materials can be stabilized and/or emulsified in solventsystems with organic or inorganic materials (organic materials can bepolymers of anionic nature, non-ionic nature or cationic nature, likepolyacrylates and polyvinyl alcohol). Suitable processes to makecore-shell systems include coating, extrusion, spray drying, interfacialpolymerization, polycondensation, simple coacervation, complexcoacervation, free radical polymerization, in situ emulsionpolymerization, matrix polymerization and combinations thereof.

Suitable characteristics for the core-shell systems include:

-   -   a) a shell thickness of from about 20 nm to about 500 nm, from        about 40 nm to about 250 nm, or from about 60 nm to about 150        nm;    -   b) a shell core ratio of from about 5:95 to about 50:50, from        about 10:90 to about 30:70, or from about 10:90 to about 15:85;    -   c) a fracture strength of from about 0.1 MPa to about 16 MPa,        from about 0.5 MPa to about 8 MPa, or even from about 1 MPa to        about 3 MPa; and    -   d) an average particle size of from about 1 micron to about 100        microns, from about 5 microns to about 80 microns, or even from        about 15 microns to about 50 microns.

Suitable deposition and/or retention enhancing coatings that may beapplied to the core-shell systems include non-ionic polymers, anionicpolymers, cationic polymers such as polysaccharides including, but notlimited to, cationically modified starch, cationically modified guar,polysiloxanes, poly diallyl dimethyl ammonium halides, copolymers ofpoly diallyl dimethyl ammonium chloride and vinyl pyrrolidone,acrylamides, imidazoles, imidazolinium halides, imidazolium halides,poly vinyl amine, copolymers of poly vinyl amine and N-vinyl formamideand mixtures thereof. In another aspect, suitable coatings may beselected from the group consisting of polyvinylformaldehyde, partiallyhydroxylated polyvinylformaldehyde, polyvinylamine, polyethyleneimine,ethoxylated polyethyleneimine, polyvinylalcohol, polyacrylates andcombinations thereof.

Suitable methods of physically reducing and/or removing any residualtype materials from the core-shell making process may be employed, suchas centrifugation. Suitable methods of chemically reducing any residualtype materials may also be employed, such as the employment ofscavengers, for example formaldehyde scavengers including sodiumbisulfite, urea, ethylene urea, cysteine, cysteamine, lysine, glycine,serine, carnosine, histidine, glutathione, 3,4-diaminobenzoic acid,allantoin, glycouril, anthranilic acid, methyl anthranilate, methyl4-aminobenzoate, ethyl acetoacetate, acetoacetamide, malonamide,ascorbic acid, 1,3-dihydroxyacetone dimer, biuret, oxamide,benzoguanamine, pyroglutamic acid, pyrogallol, methyl gallate, ethylgallate, propyl gallate, triethanol amine, succinamide, thiabendazole,benzotriazol, triazole, indoline, sulfanilic acid, oxamide, sorbitol,glucose, cellulose, poly(vinyl alcohol), partially hydrolyzedpoly(vinylformamide), poly(vinyl amine), poly(ethylene imine),poly(oxyalkyleneamine), poly(vinyl alcohol)-co-poly(vinyl amine),poly(4-aminostyrene), poly(l-lysine), chitosan, hexane diol,ethylenediamine-N,N′-bisacetoacetamide, N-(2-ethylhexyl)acetoacetamide,2-benzoylacetoacetamide, N-(3-phenylpropyl)acetoacetamide, lilial,helional, melonal, triplal, 5,5-dimethyl-1,3-cyclohexanedione,2,4-dimethyl-3-cyclohexenecarboxaldehyde,2,2-dimethyl-1,3-dioxan-4,6-dione, 2-pentanone, dibutyl amine,triethylenetetramine, ammonium hydroxide, benzylamine,hydroxycitronellol, cyclohexanone, 2-butanone, pentane dione,dehydroacetic acid, or mixtures thereof.

-   II. Molecule-Assisted Delivery (MAD): Non-polymer materials or    molecules may also serve to improve the delivery of perfume as    perfume may non-covalently interact with organic materials,    resulting in altered deposition and/or release. Non-limiting    examples of such organic materials include, but are not limited to,    hydrophobic materials such as organic oils, waxes, mineral oils,    petrolatum, fatty acids or esters, sugars, surfactants, liposomes    and even other perfume raw material (perfume oils), as well as    natural oils, including body and/or other soils.-   III. Fiber-Assisted Delivery (FAD): The choice or use of a situs    itself may serve to improve the delivery of perfume. In fact, the    situs itself may be a perfume delivery technology. For example,    different fabric types such as cotton or polyester will have    different properties with respect to ability to attract and/or    retain and/or release perfume. The amount of perfume deposited on or    in fibers may be altered by the choice of fiber, and also by the    history or treatment of the fiber, as well as by any fiber coatings    or treatments. Fibers may be pre-loaded with a perfume, and then    added to a product that may or may not contain free perfume and/or    one or more perfume delivery technologies.-   IV. Amine Assisted Delivery (AAD): The amine-assisted delivery    technology approach utilizes materials that contain an amine group    to increase perfume deposition or modify perfume release during    product use. There is no requirement in this approach to pre-complex    or pre-react the perfume raw material(s) and the amine prior to    addition to the product. In one aspect, amine-containing AAD    materials suitable for use herein may be non-aromatic, for example,    polyalkylimine, such as polyethyleneimine (PEI), or polyvinylamine    (PVAm); or aromatic, for example, anthranilates. Such materials may    also be polymeric or non-polymeric. In one aspect, such materials    contain at least one primary amine. In another aspect, a material    that contains a heteroatom other than nitrogen, for example sulfur,    phosphorus or selenium, may be used as an alternative to amine    compounds. In yet another aspect, the aforementioned alternative    compounds can be used in combination with amine compounds. In yet    another aspect, a single molecule may comprise an amine moiety and    one or more of the alternative heteroatom moieties, for example,    thiols, phosphines and selenols.-   V. Cyclodextrin Delivery System (CD): This technology approach uses    a cyclic oligosaccharide or cyclodextrin to improve the delivery of    perfume. Typically, a perfume and cyclodextrin (CD) complex is    formed. Such complexes may be preformed, formed in-situ, or formed    on or in the situs.-   VI. Starch Encapsulated Accord (SEA): SEA's are starch encapsulated    perfume materials. Suitable starches include modified starches such    as hydrolyzed starch, acid thinned starch, starch having hydrophobic    groups, such as starch esters of long chain hydrocarbons (C₅ or    greater), starch acetates, starch octenyl succinate and mixtures    thereof. In one aspect, starch esters, such as starch octenyl    succinates, are employed. Suitable perfumes for encapsulation    include the HIA perfumes, including those having a boiling point    determined at the normal standard pressure of about 760 mmHg of    275° C. or lower, an octanol/water partition coefficient P of about    2000 or higher and an odor detection threshold of less than or equal    50 parts per billion (ppb). In one aspect, the perfume may have log    P of 2 or higher.-   VII. Inorganic Carrier Delivery System (ZIC): This technology    relates to the use of porous zeolites or other inorganic materials    to deliver perfumes. Perfume-loaded zeolite may be used with or    without adjunct ingredients used for example to coat the    perfume-loaded zeolite (PLZ) to change its perfume release    properties during product storage or during use or from the dry    situs. Another example of a suitable inorganic carrier includes    inorganic tubules, where the perfume or other active material is    contained within the lumen of the nano- or micro-tubules. Monomeric    and/or polymeric materials, including starch encapsulation, may be    used to coat, plug, cap, or otherwise encapsulate the PLZ.-   VIII. Pro-Perfume (PP): This technology refers to perfume    technologies that result from the reaction of perfume materials with    other substrates or chemicals to form materials that have a covalent    bond between one or more PRMs and one or more carriers. The PRM is    converted into a new material called a pro-PRM (i.e., pro-perfume),    which then may release the original PRM upon exposure to a trigger    such as water or light. Non-limiting examples of pro-perfumes    include Michael adducts (e.g., beta-amino ketones), aromatic or    non-aromatic imines (Schiffs Bases), oxazolidines, beta-keto esters,    and orthoesters. Another aspect includes compounds comprising one or    more beta-oxy or beta-thio carbonyl moieties capable of releasing a    PRM, for example, an alpha, beta-unsaturated ketone, aldehyde or    carboxylic ester.

a.) Amine Reaction Product (ARP): For purposes of the presentapplication, ARP is a subclass or species of PP. One may also use“reactive” polymeric amines in which the amine functionality ispre-reacted with one or more PRMs, typically PRMs that contain a ketonemoiety and/or an aldehyde moiety, to form the ARP. Typically, thereactive amines are primary and/or secondary amines, and may be part ofa polymer or a monomer (non-polymer). Such ARPs may also be mixed withadditional PRMs to provide benefits of polymer-assisted delivery and/oramine-assisted delivery. Non-limiting examples of polymeric aminesinclude polymers based on polyalkylimines, such as polyethyleneimine(PEI), or polyvinylamine (PVAm). Non-limiting examples of monomeric(non-polymeric) amines include hydroxyl amines, such as 2-aminoethanoland its alkyl substituted derivatives, and aromatic amines such asanthranilates. The ARPs may be premixed with perfume or added separatelyin leave-on or rinse-off applications. In another aspect, a materialthat contains a heteroatom other than nitrogen, for example oxygen,sulfur, phosphorus or selenium, may be used as an alternative to aminecompounds. In yet another aspect, the aforementioned alternativecompounds can be used in combination with amine compounds. In yetanother aspect, a single molecule may comprise an amine moiety and oneor more of the alternative heteroatom moieties, for example, thiols,phosphines and selenols.

In one aspect, the PRMs disclosed in Table 1 and stereoisomers thereofare suitable for use in perfume delivery systems at levels, based ontotal perfume delivery system weight, of from 0.001% to about 50%, from0.005% to 30%, from 0.01% to about 10%, from 0.025% to about 5%, or evenfrom 0.025% to about 1%.

In another aspect, the perfume delivery systems disclosed herein aresuitable for use in consumer products, cleaning and treatmentcompositions, fabric and hard surface cleaning and/or treatmentcompositions, detergents, and highly compacted consumer products,including highly compacted fabric and hard surface cleaning and/ortreatment compositions (e.g., solid or fluid highly compacteddetergents) at levels, based on total consumer product weight, fromabout 0.001% to about 20%, from about 0.01% to about 10%, from about0.05% to about 5%, from about 0.1% to about 0.5%.

In another aspect, the amount of PRMs from Table 1 present in theperfume delivery systems, based on the total microcapsule and/ornanocapsule (Polymer Assisted Delivery (PAD) Reservoir System) weight,may be from about 0.1% to about 99%, from 25% to about 95%, from 30 toabout 90%, from 45% to about 90%, or from 65% to about 90%. In oneaspect, microcapsules and/or nanocapsules may comprise one or more PRMs,and stereoisomers thereof, selected from Table 1 Nos. 1, 2, 3, 4, 5, 6,7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22 and mixturesthereof. In another aspect, microcapsules and/or nanocapsules maycomprise one or more PRMs, and stereoisomers thereof, selected fromTable 1 Nos. 1, 2, 3, 4, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18,19, 20, 22 and mixtures thereof.

In one aspect, the amount of total perfume based on total weight ofstarch encapsulates and starch agglomerates (Starch Encapsulated Accord(SEA)) ranges from 0.1% to about 99%, from 25% to about 95%, from 30 toabout 90%, from 45% to about 90%, from 65% to about 90%. In one aspect,the PRMs disclosed in Table 1 and stereoisomers thereof are suitable foruse in such starch encapsulates and starch agglomerates. Such PRMs andstereoisomers thereof may be used in combination in such starchencapsulates and starch agglomerates.

In another aspect, the amount of total perfume based on total weight of[cyclodextrin-perfume] complexes (Cyclodextrin (CD)) ranges from 0.1% toabout 99%, from 2.5% to about 75%, from 5% to about 60%, from 5% toabout 50%, from 5% to about 25%. In one aspect, the PRMs disclosed inTable 1 and stereoisomers thereof are suitable for use in such[cyclodextrin-perfume] complexes. Such PRMs and stereoisomers thereofmay be used in combination in such [cyclodextrin-perfume] complexes.

In another aspect, the amount of total perfume based on total weight ofPolymer Assisted Delivery (PAD) Matrix Systems (including Silicones)ranges from 0.1% to about 99%, from 2.5% to about 75%, from 5% to about60%, from 5% to about 50%, from 5% to about 25%. In one aspect, theamount of total perfume based on total weight of a hot melt perfumedelivery system/perfume loaded plastic Matrix System and ranges from 1%to about 99%, from 2.5% to about 75%, from 5% to about 60%, from 5% toabout 50%, from 10% to about 50%. In one aspect, the PRMs disclosed inTable 1 and stereoisomers thereof are suitable for use in such PolymerAssisted Delivery (PAD) Matrix Systems, including hot melt perfumedelivery system/perfume loaded plastic Matrix Systems. Such PRMs andstereoisomers thereof may be used in various combinations in suchPolymer Assisted Delivery (PAD) Matrix Systems (including hot meltperfume delivery system/perfume loaded plastic Matrix Systems).

In one aspect, the amount of total perfume based on total weight ofAmine Assisted Delivery (AAD) (including Aminosilicones) ranges from 1%to about 99%, from 2.5% to about 75%, from 5% to about 60%, from 5% toabout 50%, from 5% to about 25%. In one aspect, the PRMs disclosed inTable 1 and stereoisomers thereof are suitable for use in such AmineAssisted Delivery (AAD) systems. Such PRMs and stereoisomers thereof maybe used in various combinations in such Amine Assisted Delivery (AAD)systems. In one aspect, an Amine Assisted Delivery (AAD) system maycomprise one or more PRMs, and stereoisomers thereof, selected fromTable 1 Nos. 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17,18, 19, 20, 21, 22 and mixtures thereof.

In one aspect, the amount of total perfume based on total weight ofAmine Reaction Product (ARP) ranges from 1% to about 99%, from 2.5% toabout 75%, from 5% to about 60%, from 5% to about 50%, from 5% to about25%. In one aspect, the PRMs disclosed in Table 1 and stereoisomersthereof are suitable for use in such Amine Reaction Product (ARP)systems. Such PRMs and stereoisomers thereof may be used in variouscombinations in such Amine Reaction Product (ARP) systems. In oneaspect, an Amine Reaction Product (ARP) system may comprise one or morePRMs, and stereoisomers thereof, selected from Table 1 Nos. 1, 2, 3, 4,5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22 andmixtures thereof. In another aspect, an Amine Reaction Product (ARP)system may comprise one or more PRMs, and stereoisomers thereof,selected from Table 1 Nos. 2, 5, 6, 21 and mixtures thereof.

The perfume delivery technologies (a.k.a., perfume delivery systems)that are disclosed in the present specification may be used in anycombination in any type of consumer product, cleaning and/or treatmentcomposition, fabric and hard surface cleaning and/or treatmentcomposition, detergent, and/or highly compact detergent.

Perfumes

The PRMs disclosed in Table 1 may be used to formulate perfumes. Suchperfumes are combinations of PRMs that may comprise a combination ofTable 1 PRMs, or one or more Table 1 PRMs and one or more additionalPRMs. When used in a perfume, the Table 1 PRMs may be employed, based ontotal perfume weight, at levels of from about 0.01% to about 50%, fromabout 0.1% to about 15%, from about 0.1% to about 10% or even from about0.5% to about 10%. Such perfumes may be utilized in variousapplications, including being applied neat to a situs or used in aconsumer product, cleaning and/or treatment composition, fabric and hardsurface cleaning and/or treatment composition, detergent, and/or ahighly compact detergent.

Adjunct Materials

For the purposes of the present invention, the non-limiting list ofadjuncts illustrated hereinafter are suitable for use in thecompositions detailed herein (e.g., consumer products, cleaning and/ortreatment compositions, fabric and hard surface cleaning and/ortreatment compositions, detergents, and/or a highly compact detergents).Such adjunct materials may be desirably incorporated in certainembodiments of the compositions, for example to assist or enhanceperformance of the composition, for treatment of the substrate to becleaned, or to modify the aesthetics of the composition as is the casewith perfumes, colorants, dyes or the like. It is understood that suchadjuncts are in addition to the components that are supplied viaApplicants' perfumes and/or perfume systems detailed herein. The precisenature of these additional components, and levels of incorporationthereof, will depend on the physical form of the composition and thenature of the operation for which it is to be used.

Suitable adjunct materials include, but are not limited to, surfactants,builders, chelating agents, dye transfer inhibiting agents, dispersants,enzymes, and enzyme stabilizers, catalytic materials, bleach activators,polymeric dispersing agents, clay soil removal/anti-redeposition agents,brighteners, suds suppressors, dyes, additional perfume and perfumedelivery systems, structure elasticizing agents, fabric softeners,carriers, hydrotropes, processing aids and/or pigments. In addition tothe disclosure below, suitable examples of such other adjuncts andlevels of use are found in U.S. Pat. Nos. 5,576,282, 6,306,812 B1 and6,326,348 B1.

Each adjunct ingredient is not essential to Applicants' compositions.Thus, certain embodiments of Applicants' compositions may not containone or more of the following adjuncts materials: bleach activators,surfactants, builders, chelating agents, dye transfer inhibiting agents,dispersants, enzymes, and enzyme stabilizers, catalytic metal complexes,polymeric dispersing agents, clay and soil removal/anti-redepositionagents, brighteners, suds suppressors, dyes, additional perfumes andperfume delivery systems, structure elasticizing agents, fabricsofteners, carriers, hydrotropes, processing aids and/or pigments.However, when one or more adjuncts are present, such adjuncts may bepresent as detailed below:

Surfactants—The compositions according to the present invention cancomprise a surfactant or surfactant system wherein the surfactant can beselected from nonionic and/or anionic and/or cationic surfactants and/orampholytic and/or zwitterionic and/or semi-polar nonionic surfactants.The surfactant is typically present at a level of from about 0.1%, fromabout 1%, or even from about 5% by weight of the cleaning compositionsto about 99.9%, to about 80%, to about 35%, or even to about 30% byweight of the cleaning compositions.

Builders—The compositions of the present invention can comprise one ormore detergent builders or builder systems. When present, thecompositions will typically comprise at least about 1% builder, or fromabout 5% or 10% to about 80%, 50%, or even 30% by weight, of saidbuilder. Builders include, but are not limited to, the alkali metal,ammonium and alkanolammonium salts of polyphosphates, alkali metalsilicates, alkaline earth and alkali metal carbonates, aluminosilicatebuilders polycarboxylate compounds. ether hydroxypolycarboxylates,copolymers of maleic anhydride with ethylene or vinyl methyl ether,1,3,5-trihydroxybenzene-2,4,6-trisulphonic acid, andcarboxymethyl-oxysuccinic acid, the various alkali metal, ammonium andsubstituted ammonium salts of polyacetic acids such as ethylenediaminetetraacetic acid and nitrilotriacetic acid, as well as polycarboxylatessuch as mellitic acid, succinic acid, oxydisuccinic acid, polymaleicacid, benzene 1,3,5-tricarboxylic acid, carboxymethyloxysuccinic acid,and soluble salts thereof.

Chelating Agents—The compositions herein may also optionally contain oneor more copper, iron and/or manganese chelating agents. If utilized,chelating agents will generally comprise from about 0.1% by weight ofthe compositions herein to about 15%, or even from about 3.0% to about15% by weight of the compositions herein.

Dye Transfer Inhibiting Agents—The compositions of the present inventionmay also include one or more dye transfer inhibiting agents. Suitablepolymeric dye transfer inhibiting agents include, but are not limitedto, polyvinylpyrrolidone polymers, polyamine N-oxide polymers,copolymers of N-vinylpyrrolidone and N-vinylimidazole,polyvinyloxazolidones and polyvinylimidazoles or mixtures thereof. Whenpresent in the compositions herein, the dye transfer inhibiting agentsare present at levels from about 0.0001%, from about 0.01%, from about0.05% by weight of the cleaning compositions to about 10%, about 2%, oreven about 1% by weight of the cleaning compositions.

Dispersants—The compositions of the present invention can also containdispersants. Suitable water-soluble organic materials are the homo- orco-polymeric acids or their salts, in which the polycarboxylic acid maycomprise at least two carboxyl radicals separated from each other by notmore than two carbon atoms.

Enzymes—The compositions can comprise one or more detergent enzymeswhich provide cleaning performance and/or fabric care benefits. Examplesof suitable enzymes include, but are not limited to, hemicellulases,peroxidases, proteases, cellulases, xylanases, lipases, phospholipases,esterases, cutinases, pectinases, keratanases, reductases, oxidases,phenoloxidases, lipoxygenases, ligninases, pullulanases, tannases,pentosanases, malanases, β-glucanases, arabinosidases, hyaluronidase,chondroitinase, laccase, and amylases, or mixtures thereof. A typicalcombination is a cocktail of conventional applicable enzymes likeprotease, lipase, cutinase and/or cellulase in conjunction with amylase.

Enzyme Stabilizers—Enzymes for use in compositions, for example,detergents can be stabilized by various techniques. The enzymes employedherein can be stabilized by the presence of water-soluble sources ofcalcium and/or magnesium ions in the finished compositions that providesuch ions to the enzymes.

Catalytic Metal Complexes—Applicants' compositions may include catalyticmetal complexes. One type of metal-containing bleach catalyst is acatalyst system comprising a transition metal cation of defined bleachcatalytic activity, such as copper, iron, titanium, ruthenium, tungsten,molybdenum, or manganese cations, an auxiliary metal cation havinglittle or no bleach catalytic activity, such as zinc or aluminumcations, and a sequestrate having defined stability constants for thecatalytic and auxiliary metal cations, particularlyethylenediaminetetraacetic acid, ethylenediaminetetra(methyl-enephosphonic acid) and water-soluble salts thereof. Suchcatalysts are disclosed in U.S. Pat. No. 4,430,243.

If desired, the compositions herein can be catalyzed by means of amanganese compound. Such compounds and levels of use are well known inthe art and include, for example, the manganese-based catalystsdisclosed in U.S. Pat. No. 5,576,282. Cobalt bleach catalysts usefulherein are known, and are described, for example, in U.S. Pat. Nos.5,597,936 and 5,595,967. Such cobalt catalysts are readily prepared byknown procedures, such as taught for example in U.S. Pat. Nos.5,597,936, and 5,595,967.

Compositions herein may also suitably include a transition metal complexof a macropolycyclic rigid ligand—abbreviated as “MRL”. As a practicalmatter, and not by way of limitation, the compositions and cleaningprocesses herein can be adjusted to provide on the order of at least onepart per hundred million of the benefit agent MRL species in the aqueouswashing medium, and may provide from about 0.005 ppm to about 25 ppm,from about 0.05 ppm to about 10 ppm, or even from about 0.1 ppm to about5 ppm, of the MRL in the wash liquor. Suitable transition-metals in theinstant transition-metal bleach catalyst include manganese, iron andchromium. Suitable MRL's herein are a special type of ultra-rigid ligandthat is cross-bridged such as5,12-diethyl-1,5,8,12-tetraazabicyclo[6.6.2]hexa-decane. Suitabletransition metal MRLs are readily prepared by known procedures, such astaught for example in WO 00/32601, and U.S. Pat. No. 6,225,464.

Methods of Use

Some of the consumer products disclosed herein can be used to clean ortreat a situs inter alia a surface or fabric. Typically at least aportion of the situs is contacted with an embodiment of Applicants'composition, in neat form or diluted in a liquor, for example, a washliquor and then the situs may be optionally washed and/or rinsed. In oneaspect, a situs is optionally washed and/or rinsed, contacted with aparticle according to the present invention or composition comprisingsaid particle and then optionally washed and/or rinsed. For purposes ofthe present invention, washing includes but is not limited to,scrubbing, and mechanical agitation. The fabric may comprise most anyfabric capable of being laundered or treated in normal consumer useconditions. Liquors that may comprise the disclosed compositions mayhave a pH of from about 3 to about 11.5. Such compositions are typicallyemployed at concentrations of from about 500 ppm to about 15,000 ppm insolution. When the wash solvent is water, the water temperaturetypically ranges from about 5° C. to about 90° C. and, when the situscomprises a fabric, the water to fabric ratio is typically from about1:1 to about 30:1.

Test Methods

It is understood that the test methods that are disclosed in the TestMethods Section of the present application should be used to determinethe respective values of the parameters of Applicants' invention as suchinvention is described and claimed herein.

(1) C Log P

The “calculated log P” (C log P) is determined by the fragment approachof Hansch and Leo (cf., A. Leo, in Comprehensive Medicinal Chemistry,Vol. 4, C. Hansch, P. G. Sammens, J. B. Taylor, and C. A. Ramsden, Eds.P. 295, Pergamon Press, 1990, incorporated herein by reference). C log Pvalues may be calculated by using the “CLOGP” program available fromDaylight Chemical Information Systems Inc. of Irvine, Calif. U.S.A.

(2) Boiling Point

Boiling point is measured by ASTM method D2887-04a, “Standard TestMethod for Boiling Range Distribution of Petroleum Fractions by GasChromatography,” ASTM International.

(3) Headspace Ratio

-   -   (a) Obtain a fragrance free consumer product formulation        (shampoo or leave-on conditioner).    -   (b) Obtain fragrance microcapsules whose water content has been        adjusted to achieve a perfume content of 25 wt % in the aqueous        slurry.    -   (c) Prepare Sample A by adding 2.0 grams of the fragrance        microcapsule aqueous slurry to 95 grams of the fragrance free        consumer product formulation. Then add 3.0 grams of deionized        water to balance the formulation to 100 grams. Age this        formulation for 1 week at 40 degrees Centigrade.    -   (d) Prepare Sample B by adding 0.50 grams of the neat fragrance        to 95 grams of fragrance free consumer product formulation. Then        add 4.5 grams of deionized water to balance the formulation to        100 grams. Age this formulation for 1 week at 40 degrees        Centigrade.

The Headspace Ratio for determining perfume leakage from a perfumedelivery system is defined as the headspace concentration of Sample Adivided by the headspace concentration of Sample B,

$\frac{H_{Sample\_ A}}{H_{Sample\_ B}},$where H_(Sample) _(_) _(A) is the headspace concentration of a consumerproduct formulation Sample A, and H_(Sample) _(_) _(B) is the headspaceconcentration of a consumer product formulation Sample B.

The Headspace Ratio for determining perfume delivery efficiency from aperfume delivery system is defined as the headspace concentration ofSample B divided by the headspace concentration of Sample A,

$\frac{H_{Sample\_ B}}{H_{Sample\_ A}},$where H_(Sample) _(_) _(A) is the headspace concentration of a consumerproduct formulation Sample A, and H_(Sample) _(_) _(B) is the headspaceconcentration of a consumer product formulation Sample B.

Solid-Phase Micro-Extraction (SPME)-Gas Chromatography/Mass Spectrometryis used to measure the level of perfume raw materials in the headspaceof products. 1.0 grams of the 1 week at 40 degrees Centigrade agedsample (shampoo or conditioner) are placed into a clean 20 ml headspacevial and allowed to equilibrate for at least 2 hours at roomtemperature.

The samples are then analyzed using the MPS2-SMPE-GC-MS analysis system(GC-02001-0153, MSD-02001-0154, MPS2-02001-0155).

Apparatus:

-   1. 20 ml headspace vial-   2. Timer.-   3. Gas Chromatograph (GC): Agilent model 6890 with a CIS-4 injector    (Gerstel, Mulheim, Germany) and MPS-2 Autosampler and TDU. For SPME    analysis, we used the split/splitless injector (not the CIS-4    injector).-   4. GC column: J&W DB-5 MS, 30 M×0.25 mm ID, 1.0 □m film thickness    obtained from J&W Scientific of Folsom, Calif., USA.-   5. Carrier gas, helium, 1.5 ml/min. flow rate.-   6. The injector liner is a special SPME liner (0.75 mm ID) from    Supelco.-   7. The Detector is a model 5973 Mass Selective Detector obtained    from Agilent Technologies, Inc., Wilmington, Del., USA having a    source temperature of about 230° C., and a MS Quad temperature of    about 150° C.    Analysis Procedure:    -   1. Transfer sample to proper sample tray and proceed with        SPME-GC-MS analysis.    -   2. Start sequence of sample loading and analysis. In this step,        the sample is allowed to equilibrate for at least two hours on        the auto sampler tray, then sampled directly from the tray. The        SPME fiber assembly is DVB/CAR/PDMS (50/30 um, 24 ga, 1 cm        length). Sampling time is 5 minutes.    -   3. Injector temperature is at 260 C.    -   4. Then GC-MS analysis run is started. Desportion time is 5        minutes.    -   5. The following temperature program is used:        -   i) an initial temperature of about 50° C. which is held for            3 minutes,        -   ii) increase the initial temperature at a rate of about 6°            C./min until a temperature of about 250° C. is reached, then            25° C./min to 275° C., hold at about 275° C. for 4.67            minute.    -   6. Perfume compounds are identified using the MS spectral        libraries of John Wiley & Sons and the National Institute of        Standards and Technology (NIST), purchased and licensed through        Hewlett Packard.    -   7. Chromatographic peaks for specific ions are integrated using        the Chemstation software obtained from Agilent Technologies,        Inc., Wilmington, Del., USA.    -   8. The ratio for each PRM is calculated by dividing the peak        area for the perfume raw material in Sample A by the peak area        in Sample B.    -   9. Each ratio is then weighted by that perfume raw material's        weight composition in the perfume.    -   10. The Headspace Ratio is calculated as the sum of the        individual perfume raw material ratios obtained in step 9.

(4) Perfume Leakage can Also be Evaluated Via % Liquid-Liquid Extractionand Gas Chromatographic-Mass Spectrometric Analysis

When determining the % perfume leakage from Perfume Microcapsules inliquid detergent, a fresh sample of liquid detergent with equal level offree perfume (without Perfume Microcapsules) must also be analyzed inparallel for reference.

1. Preparation of an Internal Standard Solution

-   -   Stock solution of tonalid: Weigh 70 mg tonalid and add 20 ml        hexane p.a.    -   Internal Standard Solution solution: Dilute 200 μl of stock        solution in 20 ml hexane p.a.    -   Mix to homogenize

2. Perfume Extraction from Liquid Detergent without PerfumeMicrocapsules (Reference)

-   -   Weigh 2 g of liquid detergent product into an extraction vessel    -   Add 2 ml of Internal Standard Solution and close vessel    -   Extract perfume by gently turning the extraction vessel        upside-down for 20 times (manually)    -   Add spoon tip of Sodium Sulphate    -   After separation of layers, immediately transfer hexane-layer        into Gas Chromatograph auto sampler-vial and cap vial    -   Inject splitless (1.5 μl) into Gas Chromatograph injection-port    -   Run Gas Chromatographic-Mass Spectrometric analysis

3. Perfume Extraction from Liquid Detergent with Perfume Microcapsules

-   -   Weigh 2 g of liquid detergent product into an extraction vessel    -   Add 2 ml of Internal Standard Solution and close vessel    -   Extract perfume by gently turning the extraction vessel        upside-down for 20 times (manually)    -   Add spoon tip of Sodium Sulphate    -   After separation of layers, immediately transfer hexane-layer        into Gas Chromatograph auto sampler-vial and cap vial    -   Inject splitless (1.5 μl) into Gas Chromatograph injection-port    -   Run Gas Chromatographic-Mass Spectrometric analysis

4. Calculation

-   -   The perfume leakage from capsules per individual Perfume Raw        Material:        % perfume leakage=((Area Perfume Raw Material caps×Area Internal        Standard Solution ref×Weight ref)/(Area Internal Standard        Solution caps×Area Perfume Raw Material ref×Weight caps))×100

(5) Odor Detection Threshold (ODT)

Determined using a gas chromatograph. The gas chromatograph iscalibrated to determine the exact volume of material injected by thesyringe, the precise split ratio, and the hydrocarbon response using ahydrocarbon standard of known concentration and chain lengthdistribution. The air flow rate is accurately measured and, assuming theduration of human inhalation to last 12 seconds, the sampled volume iscalculated. Since the precise concentration at the detector at any pointin time is known, the mass per volume inhaled is known, and hence theconcentration of material.

For example, to determine whether a material has a threshold below 50parts per bullion, solutions are delivered to the sniff port at thecalculated concentration. A panelist sniffs the GC effluent andidentifies the retention time when odor is noticed. The average among 6panelists determines the threshold of noticeability. The necessaryamount of analyte is injected into the column to achieve a 50 parts perbillion concentration at the detector. Typical gas chromatographparameters for determining odor detection thresholds are listed below:

-   -   GC: 5890 Series II with FID detector, 7673 Autosampler    -   Column: J&W Scientific DB-1    -   Length: 30 meters, 0.25 millmeter inside diameter, 1 micrometer        film thickness    -   Method:        -   split injection: 17/1 split ratio        -   Autosampler: 1.13 microliters per injection        -   Column flow: 1.10 milliLiters per minute        -   Air Flow: 345 milliLiters per minute        -   Inlet Temperature: 245 degrees Centigrade        -   Detector Temperature: 285 degrees Centigrade        -   Initial Temperature=50 degrees Centigrade, 5 degrees            Centigrade per minute ramp rate, final temperature=280            degrees Centigrade, Final time=6 minutes        -   Leading assumptions: 12 seconds per sniff, GC air adds to            sample dilution

EXAMPLES

While particular embodiments of the present invention have beenillustrated and described, it would be obvious to those skilled in theart that various other changes and modifications can be made withoutdeparting from the spirit and scope of the invention. It is thereforeintended to cover in the appended claims all such changes andmodifications that are within the scope of this invention.

Example 1 Synthesis of Table 1 Molecules

Synthesis of table 1 molecule No. 14:

Preparation of 1-(2,4,6-trimethyl-cyclohex-3-enyl)-propan-1-one:1-(2,4,6-Trimethyl-cyclohex-3-enyl)-propan-1-ol (182 g, 1.0 mol)dissolved in acetone (400 mL) was added dropwise to a solution ofchromium trioxide (CrO₃, 108 g, 1.08 mol) in aqueous sulfuric acid(H₂SO₄, 400 mL, 172 g in water) at −10° C. The resulting mixture wasaged for 2 hours as the mixture warmed to 0° C. The mixture was thendiluted with water and extracted with toluene. The organic layer wasconcentrated by rotary evaporation and distilled via fractionation toprovide 1-(2,4,6-trimethyl-cyclohex-3-enyl)-propan-1-one (113 g, 63%yield) as a colorless liquid.

¹H NMR and ¹³C NMR data matched those reported previously (See, J. Am.Chem. Soc. 1997, 119, pages 3507-3512).

Synthesis of table 1 molecule No. 2:

Preparation of 3-methyl-2-methylene-butyraldehyde: Di-n-butylamine (75g, 0.58 mol) and acetic acid (70 g, 1.16 mol) were mixed in a 5 L roundbottom flask. Formaldehyde (1.411 Kg, 17.4 mol) was then added and theresulting mixture was heated to 50° C. Isovaleraldehyde (1 Kg, 11.6 mol)was fed into the reaction mixture at 50° C. for over 2.5 hours. Afterthe feed was completed, gas chromatograph analysis (GC analysis)indicated that the reaction was 92% complete. The reaction mixturecontaining 3-methyl-2-methylene-butyraldehyde was cooled to roomtemperature and washed with a saturated sodium carbonate solution.

Preparation of 1-isopropyl-2,4-dimethyl-cyclohex-3-enecarbaldehyde:Methylpentadiene (428 g, 5.1 mol) was placed in a stainless-steelautoclave containing the reaction mixture of3-methyl-2-methylene-butyraldehyde (500 g, 5.1 mol, obtained as detailedabove) and heated to 200° C. The reaction was monitored by GC analysisand stopped when a 75% conversion rate was observed. The resultingmixture was then cooled to room temperature and removed from theautoclave. The crude product1-isopropyl-2,4-dimethyl-cyclohex-3-enecarbaldehyde was dissolved intoluene and azeotroped to dryness under a reduced pressure.

Preparation of (1-isopropyl-2,4-dimethyl-cyclohex-3-enyl)-methanol:Isopropylmagnesium chloride ((CH₃)₂HCMgCl) in tetrahydrofuran (THF) (1.6L, 3.2 mol) was loaded into a flame-dried 5 L round bottom flask.Additional THF (1 L) was added.1-Isopropyl-2,4-dimethyl-cyclohex-3-enecarbaldehyde (obtained asdetailed above) was then fed for over 2 hours at 0° C. under nitrogen.The reaction mixture was aged at 0° C. for another 3 hours and thenquenched by pouring the reaction mixture onto a sulfuric acid solution(10%) on crushed ice. The organic layer was separated, washed withsodium carbonate solution, and distilled to provide(1-isopropyl-2,4-dimethyl-cyclohex-3-enyl)-methanol.

Preparation of 4-isopropyl-1,5-dimethyl-2-oxa-bicyclo[2.2.2]octane:(1-Isopropyl-2,4-dimethyl-cyclohex-3-enyl)-methanol (165 g, 0.9 mol,obtained as detailed above) was dissolved in toluene withmethanesulfonic acid (MSA, 5 g, 0.05 mol). The resulting solution washeated to 70° C. and aged at 70° C. for 2 hours. GC analysis showed thecompletion of cyclization. The reaction mixture was cooled to roomtemperature, washed with sodium carbonate solution, and distilled toprovide 4-isopropyl-1,5-dimethyl-2-oxa-bicyclo[2.2.2] octane.

Synthesis of table 1 molecule No. 3:

Preparation of 3,4-dimethyl-2-methylene-pentanal: Dibutylamine (34 g),acetic acid (15.78 g), and formaldehyde (230 g) were charged to areaction flask and heated to 70° C. 3,4-Dimethyl-pentanal (500 g) wasfed over 2 hours and aged for another hour. The reaction mixture wascooled down and toluene (200 mL) was added. The reaction mixture wassequentially washed with water (2 L), sodium carbonate solution (1 L),and brine (1 L) to provide the crude product3,4-dimethyl-2-methylene-pentanal.

Preparation of1-(1,2-dimethyl-propyl)-3-methyl-cyclohex-3-enecarbaldehyde:3,4-Dimethyl-2-methylene-pentanal (550 g, obtained as detailed above)and 393 g of isoprene were charged to a Parr Bomb, heated to 160° C.,and aged for 12 hours. The rushed over material provided ˜32% recoveryof 1-(1,2-dimethyl-propyl)-4-methyl-cyclohex-3-enecarbaldehyde (415 g).

Preparation of[1-(1,2-dimethyl-propyl)-4-methyl-cyclohex-3-enyl]-methanol:1-(1,2-Dimethyl-propyl)-4-methyl-cyclohex-3-enecarbaldehyde (415 g) andmethanol (300 mL) were charged into a reaction flask. Sodium borohydride(15 g) was added slowly and the temperature was kept at 35° C. with anice bath. The reaction mixture was aged for 2 hours and quenched ontoHCl (42 g) and ice and extracted with toluene. The reaction mixture waswashed until neutral. The rushed over material provided the recovery of[1-(1,2-dimethyl-propyl)-4-methyl-cyclohex-3-enyl]-methanol (366 g).

Preparation of4-(1,2-dimethyl-propyl)-1-methyl-2-oxa-bicyclo[2.2.2]octane:[1-(1,2-Dimethyl-propyl)-4-methyl-cyclohex-3-enyl]-methanol (268 g,obtained as detailed above), MSA (10 g), and toluene (300 mL) werecharged to a 2 L reaction flask, heated to 60° C., and aged for 12hours. The reaction mixture was cooled, washed with saturated sodiumcarbonate solution, and distilled to provide4-(1,2-dimethyl-propyl)-1-methyl-2-oxa-bicyclo[2.2.2]octane (146 g).

Synthesis of table 1 molecule No. 4:

Preparation of 2-[3-methyl-butylidene]-cyclopentanone: Water (1.9 L) andsodium hydroxide (NaOH, 40 g, 50% caustic) were charged in a flask andheated to 80° C. A premix of cyclopentanone (840 g, 10 mol) andisovaleraldehyde (1.05 Kg, 12 mol) was slowly fed for over 5 hours. Thereaction mixture was aged at 80° C. for another 30 minutes, cooled toroom temperature, and quenched with acetic acid (120 g, 2 mol). Arushover process provided the crude product2-[3-methyl-butylidene]-cyclopentanone.

Preparation of 2-(3-methyl-butyl)-cyclopent-2-enone:2-(3-Methyl-butyllidene)-cyclopentanone (1.093 Kg, 7.19 mol, obtained asdetailed above), acetic anhydride (300 mL, 3.17 mol), p-toluenesulfonicacid (PTSA, 10 g), and toluene (500 mL) were charged into a flask andheated to 120-130° C. When gas chromatography analysis indicated thecompletion of the reaction, the reaction mixture was cooled to roomtemperature and quenched with Na₂CO₃ solution (100 mL). The resultingmixture was washed twice with brine (1 L). A rushover process providedthe crude product 2-(3-methyl-butyl)-cyclopent-2-enone.

Preparation of 2-(3-methyl-butyl)-3-vinyl-cyclopentanone: Vinylmagnesiumchloride (H₂CHCClMg, 1 L) and cuprous chloride were charged to a driedflask under nitrogen and cooled to −25° C. with a dry ice bath. Theresulting mixture was fed with 2-(3-methyl-butyl)-cyclopent-2-enone (226g, 1.49 mol, obtained as detailed above) slowly for over 4 hours, agedfor another 4 hours, and allowed to warm to 0° C. The reaction mixturewas then poured into acetic acid solution and washed to neutral withsaturated Na₂CO₃ solution. The distillation process provided the product2-(3-methyl-butyl)-3-vinyl-cyclopentanone.

Synthesis of carboxylic acids used for the synthesis of table 1 moleculeNo. 5:

Preparation of 2,5,5-trimethyl-2-propyl-[1,3]dioxane: 2-Pentanone,2,2-dimethyl-propane-1,3-diol, and a catalytic amount ofp-toluenesulfonic acid (PTSA) were refluxed in toluene to provide acrude product. Distillation provided the product2,5,5-trimethyl-2-propyl-[1,3]dioxane.

¹HNMR: 3.54 ppm (d, 2H, J=11.1 Hz), 3.44 ppm (d, 2H, J=10.7 Hz), 1.67ppm (m, 2H), 1.44 ppm (m, 2H), 1.35 ppm (s, 3H), 1.00 ppm (s, 3H), 0.93ppm (t, 3H, J=7.4 Hz), 0.90 ppm (s, 3H)

Synthesis of table 1 molecule No. 6:

Preparation of 1,2,4-trimethyl-bicyclo[2.2.1]heptane-2-carboxylic acid:A solution of fenchol (179 g) in formic acid (90%, 157 g) was added tosulfuric acid (98%) at 0-15° C. with slow stirring. Upon finish, thereaction mixture was stirred for another 2 hours and then poured intoice. The reaction mixture was extracted three times with toluene (100mL). The organic phases were combined and extracted with aqueous sodiumhydroxide (10%, 500 mL). The organic phase was discarded. The aqueousphase was acidified with sulfuric acid till pH<1, and then extractedwith toluene. The resulting organic phase was concentrated to provide1,2,4-trimethyl-bicyclo[2.2.1]heptane-2-carboxylic acid (135 g, 73%yield) as a white solid.

Preparation of 1,2,4-trimethyl-bicyclo[2.2.1]heptane-2-carboxylic acidmethyl ester: 1,2,4-Trimethyl-bicyclo[2.2.1]heptane-2-carboxylic acid(obtained as detailed above) was dissolved in methylene chloride (50mL), and added dropwise to thionyl chloride (100 mL) at 50° C. After 1hour, excessive thionyl chloride was distilled out and methanol (100 mL)was added. The reaction mixture was stirred overnight and then pouredinto saturated aqueous sodium bicarbonate. The resulting mixture wasextracted with toluene and the organic phase was distilled to provide1,2,4-trimethyl-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester (65g, 45% yield).

Synthesis of table 1 molecule No. 7:

Preparation of 8-hydroxy-2,6-dimethyl-nona-2,6-diene: Methyl lithium intetrahydrofuran (THF) (1.6 L, 1 M) was charged to a flame dried 3 Lreaction flask equipped with a thermometer, a mechanical stirrer,condenser, and an addition funnel. Citral was added dropwise for over2-2.5 hours. The reaction mixture was aged until the conversion rate wasgreater than 90%. The reaction mixture was cooled to lower than 30° C.and quenched by the slow addition of HCl (pH<5. 10%). The aqueous phasewas extracted three times with toluene (100 mL) and the extracts wereadded to the crude reaction mixture. The crude reaction mixture was thenwashed with saturated sodium bicarbonate (500 mL) followed by saturatedsalt solution and dried over anhydrous sodium sulphate. The crudereaction mixture was concentrated. The solvents were recovered via arotary evaporator to provide 8-hydroxy-2,6-dimethyl-nona-2,6-diene.

Preparation of 8-ethoxy-2,6-dimethyl-nona-2,6-diene: THF (500 mL) andsodium hydride (60%, 52 g, 1.3 mol) were charged to a flame dried 2 Lreaction flask equipped with a thermometer, a mechanical stirrer, acondenser, and an addition funnel. 8-Hydroxy-2,6-dimethyl-nona-2,6-diene(obtained as detailed above) was added dropwise while allowing thetemperature to rise no higher than 50° C. After the addition wascompleted, the reaction mixture was aged for 1 hour. Ethyl bromide (142g, 1.3 mol.) was added dropwise for over 2 hours. The reaction mixturewas then heated to 60° C. and aged until the conversion rate was shownto be over 90%. The reaction mixture was cooled to lower than 30° C. andquenched by the slow addition of HCl (pH<5, 10%). The layers were split.The aqueous phase was extracted three times with toluene (100 mL). Theextracts were added to the crude reaction mixture, which was then washedwith saturated sodium bicarbonate followed by saturated salt solutionand dried over anhydrous sodium sulphate. The crude reaction mixture wasconcentrated. The solvents were recovered via a rotary evaporator.Fractional distillation provided the compound8-ethoxy-2,6-dimethyl-nona-2,6-dien with a boiling point of 125° C. at apressure of 4.5 mmHg.

¹HNMR: 5.06-5.13 ppm (m, 2H); 4.09-4.18 ppm (m, 1H); 3.43-3.53 ppm (m,1H); 3.27-3.37 ppm (m, 1H); 2.00-2.16 ppm (m, 4H); 1.60-1.74 ppm (m,9H); 1.15-1.20 ppm (m, 6H).

Synthesis of table 1 molecule No. 8:

Preparation of 2,6-dimethyl-2-(2-methyl-allyl)-cyclohexanone:2,6-Dimethyl-cyclohexanone (1 kg, 4 mol), trimethyl orthoformate (TMOF,880 g), and methanol (800 mL) were charged to a 5 L reaction flask. HClwas added quickly. Reaction exothermed and the temperature increasedfrom 14° C. to 20° C. The reaction mixture was heated to 60° C. and agedfor 7 hours. When the reaction was about 75% complete, the reactionmixture was quenched with NaOCH₃ (25%, 25 g), heated to 90° C., andapplied to a Bidwell-Sterling trap. The reaction mixture was then cooledto room temperature followed by sequential addition of methallyl alcohol(1.25 Kg, 8.5 moles), HOAc (50 g), and methane sulfonic acid (MSA, 10g). The resulting mixture was heated to 110° C., applied to aBidwell-Sterling trap, and aged for 4 hours until gas chromatographanalysis indicated that the reaction was 95% completed. The reactionmixture was then cooled and washed with saturated sodium carbonatesolution (3 L) to provide the crude product2,6-dimethyl-2-(2-methyl-allyl)-cyclohexanone.

Preparation of 2,2,3a,7-tetramethyl-octahydro-benzofuran: A 3 L reactionflask was charged with vitride (325 g, 0.9 mol) and toluene (500 mL),heated to 100° C., fed with2,6-dimethyl-2-(2-methyl-allyl)-cyclohexanone (200 g, 1.1 mol, obtainedas detailed above) for over 2 hours, and aged for another 2 hours. Afterthe reaction completed, the reaction mixture was cooled to roomtemperature, quenched with IPA (100 mL). NaOH (50%, 300 g) and water(200 mL) were then added, heated to 80° C., and aged for another hour.The reaction mixture was cooled to room temperature and more water (200mL) was added. Layers were split to dispose the aqueous waste. Theorganic layer was charged back to the flask. Toluene (300 mL) was addedand water was removed with a Bidwell-Sterling trap through azeotrope.The resulting mixture was cooled to 50° C. MSA (28 g, 0.3 mol) was addedand the reaction mixture was heated to reflux. The consumption of thestarting material was indicated after 3 hours. The resulting mixture wasthen cooled to room temperature and washed with saturated sodiumcarbonate solution (1 L) followed by brine (1 L). Distillation andfractionation provided the product2,2,3a,7-tetramethyl-octahydro-benzofuran (125 g).

Synthesis of table 1 molecule No. 9:

Preparation of 3a-isopropyl-2,6-dimethyl-octahydro-benzofuran: Menthone(500 g), trimethylorthoformate (377 g) and methanol (400 mL) werecharged to a 3 L reaction flask. In one portion, hydrochloric acid (3 g)was added and the mixture exothermed from 22° C. to 40° C. The reactionmixture was aged 6 hours and quenched with sodium methoxide solution (35g). Low boiling materials were removed while the reaction mixture washeated to 90° C. Allyl alcohol (404 g) and acetic acid (195 g) wereadded and the reaction mixture was heated to 160° C. The reactionmixture was held at 160° C. for 3 hours, cooled to 25° C., and washedwith brine (500 mL). The crude product was distilled to provide amixture of allyl menthone isomers.

Red-Al® (397 g) was charged to a 2 L reaction flask and heated to 55° C.Allyl menthone isomers (248 g, obtained in above) were fed into theflask and the reaction was allowed to exotherm to 70° C. The reactionmixture was aged for 8 hours and quenched with isopropanol (100 mL)followed by aqueous sodium hydroxide solution (50%, 307 g). Theresulting organic layer was washed with brine (500 mL). The crudealcohol was distilled to provide a mixture of allyl menthol isomers.

Allyl menthol isomers (200 g, obtained in above), toluene (500 mL), andmethanesulfonic acid (MSA, 5 g) were charged to 1 L reaction flask. Thereaction mixture was heated to 80° C., aged for 8 hours, then cooled to22° C., and washed with aqueous sodium carbonate solution (10%, 300 mL).The resulting crude mixture was purified by distillation to afford3a-isopropyl-2,6-dimethyl-octahydro-benzofuran.

Synthesis of table 1 molecule No. 10:

Preparation of 4-cyclopropylmethoxymethyl-5-methyl-cyclohexene: Areaction flask was charged with tetrahydrofuran (THF, 500 mL) and sodiumamide (NaNH₂, 100 g, 2.6 mol) and heated to reflux (˜65° C.).(6-Methyl-cyclohex-3-enyl)-methanol (300 g, 2.3 mol) was fed in. Thereaction mixture was aged for a half-hour. Bromomethyl-cyclopropane (526g, 3.9 mol) was then fed for over 2 hours at the reflux temperature. Thereaction was monitored by gas chromatography. A sample the reactionmixture was quenched in isopropyl alcohol, water, and toluene. After thefeed of bromomethyl-cyclopropane was completed, the reaction was agedfor a total of 6 hours. The reaction mixture was then cooled to 10° C.and quenched with isopropyl alcohol (100 mL), water (1 L), and toluene(500 mL). On the work-up, the reaction mixture was acidified with HCl(300 mL) and washed with sodium carbonate solution (5%, 500 mL) in aseparatory funnel followed with warm H₂O until the pH was neutral.Distillation of the resulting mixture provided the product4-cyclopropylmethoxymethyl-5-methyl-cyclohexene.

Synthesis of table 1 molecule No. 11:

Preparation of cyclopropanecarboxylic acid 1-methyl-hexyl ester:2-Heptanol (200 g, 1.72 mol) and cyclopropanecarboxylic acid (163 g,1.90 mol) were added into toluene (500 mL), followed byp-toluenesulfonic acid (3.2 g, 0.0172 mol). The reaction mixture washeated to reflux for 6 hours, cooled to room temperature, and quenchedwith aqueous sodium bicarbonate (1 L). The reaction mixture was thenwashed with brine (0.5 L) and dried over sodium sulfate (50 g). Thesolvent was removed and the reaction mixture was distilled to providethe product cyclopropanecarboxylic acid 1-methyl-hexyl ester (253 g).

Synthesis of table 1 molecule No. 12:

Preparation of 3-isopropyl-6-methyl-2-propenyl-tetrahydro-pyran:6-Methyl-hept-5-en-2-ol (512 g, 3.8 mol, 96%), toluene (750 ml), andp-toluenesulfonic acid (pTSA, 2.6 g) were charged in a flask and heatedto 122° C. Crotonaldehyde (350 g, 5 mol) was fed into the mixture forover 3-4 hours at reflux. Water was removed with a Bidwell-Sterlingtrap. The reaction mixture was aged for 1 hour. Standard addition andgas chromatography (GC) analysis indicated that about 11% of thestarting material 6-methyl-hept-5-en-2-ol was left. Additionalcrotonaldehyde (35 g, 0.5 mol) was added. The reaction mixture was atreflux for another 45 minutes. About 70 ml water was collected and thefinal temperature was about 118° C. GC analysis indicated that about 8%of the starting material 6-methyl-hept-5-en-2-ol was left. The reactionmixture was quenched with water and wash one time with dilute carbonatesolution. The consequent rushover process provided the product3-isopropyl-6-methyl-2-propenyl-tetrahydro-pyran (493 g) with a boilingpoint of 109 C at a pressure of 25 mmHg.

Synthesis of table 1 molecule No. 13:

Preparation of acetic acid 3-isopropyl-1,2-dimethyl-cyclopentyl ester:Trans-dihydroplinol (165 g) and dimethylaminopyridine (2 g) were chargedinto a 1 L round bottom flask and heated to 80° C. Acetic anhydride (143g) was added to the resulting mixture and was stirred at the sametemperature until the majority of the starting material was consumed.The reaction mixture was then cooled to room temperature, washed withwater and sodium carbonate, and extracted with toluene. The organicsolvents were removed in vacuo and fractional distillation provided theproduct acetic acid 3-isopropyl-1,2-dimethyl-cyclopentyl ester (45 g,21% yield).

Synthesis of table 1 molecule No. 1:

Preparation of 4-(2,4-dimethyl-cyclohex-3-enylidene)-butan-2-one:Ketoester (780 g) was added into a 2 L round bottom flask and heated to200° C. Water (2 equivalents) was added drop-wise and the lightersolvent was removed via a Bidwell-Sterling trap. The reaction mixturewas then cooled to room temperature. The crude product was dried overanhydrous sodium sulfate. Fractional distillation provided product4-(2,4-dimethyl-cyclohex-3-enylidene)-butan-2-one (231 g).

Synthesis of table 1 molecule No. 15:

Preparation of 4-methyl-cyclohex-4-ene-1,2-dicarboxylic acid dimethylester: Isoprene (350 g, 5.1 mol) and dimethyl maleate (741 g, 5.1 mol)were loaded into a stainless steel autoclave. The autoclave was sealedand heated to 150° C. The temperature of the autoclave increased to 195°C. due to the heat of the reaction. The temperature was held at 160° C.for 1 hour. Gas chromatography (GC) analysis indicated the completion ofthe reaction. The autoclave was then cooled to room temperature. Simpledistillation of the resulting mixture provided4-methyl-cyclohex-4-ene-1,2-dicarboxylic acid dimethyl ester (725 g, 3.4mol, 66% yield) as a light yellow liquid.

Preparation of2-[6-(1-hydroxy-1-methyl-ethyl)-4-methyl-cyclohex-3-enyl]-propan-2-ol:Methylmagnesium chloride (MeMgCl, 3 M, 4.6 L, 13.6 mol) andtetrahydrofuran (THF, 2.5 L) were placed in a 12 L round bottom flaskunder nitrogen. The resulting solution was cooled to 0-10° C. using anautomatic dry ice bath. The 4-methyl-cyclohex-4-ene-1,2-dicarboxylicacid dimethyl ester (725 g, 3.4 mol, obtained as detailed above) wasthen fed into the reaction flask under nitrogen while the temperaturewas held steady. The completion of the reaction was monitored by GCanalysis. After the feed was complete, the reaction mixture was quenchedby pouring onto sulfuric acid solution (10%) and ice. The resultinglayers were then split and the organic layers were washed with saturatedsodium carbonate solution. The resulting mixture was then reduced involume using a rotovap to provide the crude product2-[6-(1-hydroxy-1-methyl-ethyl)-4-methyl-cyclohex-3-enyl]-propan-2-ol(720 g, 3.3 mol).

Preparation of1,1,3,3,5-pentamethyl-1,3,3a,4,7,7a-hexahydro-isobenzofuran:2-[6-(1-Hydroxy-1-methyl-ethyl)-4-methyl-cyclohex-3-enyl]-propan-2-ol(720 g, 3.3 mol, obtained as detailed above) was loaded into a roundbottom flask fitted with a Bidwell-Sterling trap and dissolved intoluene (1 L). An acid catalyst p-toluenesulfonic acid (pTSA, 40 g, 0.18mol) was added and the mixture was heated to reflux. The reflux wasmaintained for 1.5 hours. Water was collected in the Bidwell-Sterlingtrap during this period. GC analysis indicated the completion of thereaction. The resulting mixture was reduced in volume and purified byfractional distillation to provide1,1,3,3,5-pentamethyl-1,3,3a,4,7,7a-hexahydro-isobenzofuran (60 g, 9%yield).

Synthesis of table 1 molecule No. 16:

Preparation of undec-8-ene-2,5-diol: But-3-yn-2-ol was added into asolution of ethyl magnesium bromide (EtMgBr) in tetrahydrofuran (THF).Hept-4-enal was then dropped into the mixture at room temperature andaged for 2 hours. The rush over process provided the productundec-8-en-3-yne-2,5-diol.

Preparation of undec-8-ene-2,5-diol: Undec-8-en-3-yne-2,5-diol (obtainedas detailed above) was hydrogenated under hydrogen and 10 percentpalladium on barium sulphate and quinoline. The rush over processprovided the product undec-8-ene-2,5-diol.

Preparation of 2-(hex-3-enyl)-5-methyl-tetrahydro-furan:Undec-8-ene-2,5-diol (obtained as detailed above) was heated to 150° C.with KHSO4. The resulting mixture was distilled to provide the product2-(hex-3-enyl)-5-methyl-tetrahydro-furan.

Synthesis of table 1 molecule No. 17:

3-sec-Butyl-1,5-dimethyl-2-oxa-bicyclo[2.2.2]octane may be prepared bythe process disclosed in U.S. Pat. No. 4,197,328 to Schmitt et al.

Synthesis of table 1 molecule No. 18:

1-(6-Isopropyl-2-methyl-cyclohex-3-enyl)-ethanone may be prepared by theprocess disclosed in European Patent Application No. 0231556 (A1) to Vander Weerdt et al.

Synthesis of table 1 molecule No. 19:

1-(6-Isopropyl-4-methyl-cyclohex-3-enyl)-ethanone may be prepared by theprocess disclosed in U.S. Pat. No. 4,524,020 to Spreker at al.

Synthesis of table 1 molecule No. 20:

4-(3-Methoxy-1-methyl-propyl)-1-methyl-cyclohexene may be prepared bythe process disclosed in European Patent Application No. 53716 A1 toSchaper et al.

Synthesis of table 1 molecule No. 21:

3-(1,1-Dimethoxy-ethyl)-1,1-dimethyl-cyclohexane may be prepared by theprocess disclosed in U.S. Pat. No. 4,933,320 to Spreker et al.

Synthesis of table 1 molecule No. 22:

2,4-Dimethyl-2-(4-methyl-pent-3-nyl)-[1,3]dioxolane may be prepared bythe process disclosed in Huaxue Yanjiu Yu Yingyong, 2003, pp 229-230, toPeng, A., Xia, M., Jin, X.

Example 2 Preformed Amine Reaction Product

The following ingredients are weighted off in a glass vial:

-   -   1. 50% of the perfume material comprising one or more Table 1        PRMs    -   2. 50% of Lupasol WF (CAS#09002-98-6) from BASF, is put at        60° C. in warm water bath for 1 hour before use.

Mixing of the two ingredients is done by using the Ultra-Turrax T25Basic equipment (from IKA) during 5 minutes. When the mixing is finishedthe sample is put in a warm water bath at 60° C. for ±12 hours. Ahomogenous, viscous material is obtained.

In the same way as described above different ratios between thecomponents can be used:

Weight % Perfume Material 40 50 60 70 80 Lupasol WF 60 50 40 30 20

Example 3 84 wt % Core/16 wt % Wall Melamine Formaldehyde (MF) Capsule(PAD Reservoir System

25 grams of butyl acrylate-acrylic acid copolymer emulsifier (ColloidC351, 25% solids, pka 4.5-4.7, (Kemira Chemicals, Inc. Kennesaw, Ga.U.S.A.) is dissolved and mixed in 200 grams deionized water. The pH ofthe solution is adjusted to pH of 4.0 with sodium hydroxide solution. 8grams of partially methylated methylol melamine resin (Cymel 385, 80%solids, (Cytec Industries West Paterson, N.J., U.S.A.)) is added to theemulsifier solution. 200 grams of perfume oil comprising one or moreTable 1 PRMs is added to the previous mixture under mechanical agitationand the temperature is raised to 50° C. After mixing at higher speeduntil a stable emulsion is obtained, the second solution and 4 grams ofsodium sulfate salt are added to the emulsion. This second solutioncontains 10 grams of butyl acrylate-acrylic acid copolymer emulsifier(Colloid C351, 25% solids, pka 4.5-4.7, Kemira), 120 grams of distilledwater, sodium hydroxide solution to adjust pH to 4.8, 25 grams ofpartially methylated methylol melamine resin (Cymel 385, 80% solids,Cytec). This mixture is heated to 70° C. and maintained overnight withcontinuous stirring to complete the encapsulation process. 23 grams ofacetoacetamide (Sigma-Aldrich, Saint Louis, Mo., U.S.A.) is added to thesuspension. An average capsule size of 30 um is obtained as analyzed bya Model 780 Accusizer.

Example 4 Process of Making a Polymer Assisted Delivery (PAD) MatrixSystem

A mixture comprising 50% of a perfume composition comprising one or moreTable 1 PRMs, 40% of carboxyl-terminated Hycar®1300X18(CAS#0068891-50-9) from Noveon, (put at 60° C. in warm water bath for 1hour before mixing) and 10% of Lupasol® WF(CAS#09002-98-6) from BASF(put at 60° C. in warm water bath for 1 hour before mixing). Mixing isachieved by mixing for five minutes using a Ultra-Turrax T25 Basicequipment (from IKA). After mixing, the mixture is put in a warm waterbath at 60° C. for ±12 hours. A homogenous, viscous and sticky materialis obtained.

In the same way as described above different ratios between thecomponents can be used:

Weight % Perfume composition 40 50 60 70 80 Lupasol ® WF 12 10 8 6 4Hycar ® 48 40 32 24 16 CTBN1300X18 Weight % Perfume composition 50 50 5050 50 50 50 50 Lupasol ® WF 2.5 5 7.5 10 12.5 15 17.5 20 Hycar ® 47.5 4542.5 40 37.5 35 32.5 30 CTBN 1300X18

Example 5 Product Formulation

Non-limiting examples of product formulations containing PRMs disclosedin the present specification perfume and amines summarized in thefollowing table.

EXAMPLES (% wt) XI XII XIII XIV XV XVI XVII XVIII XIX XX FSA ^(a) 1416.47 14 12 12 16.47 — — 5 5 FSA ^(b) — 3.00 — — — FSA ^(c) — — 6.5 — —Ethanol 2.18 2.57 2.18 1.95 1.95 2.57 — — 0.81 0.81 Isopropyl — — — — —— 0.33  1.22 — — Alcohol Starch ^(d) 1.25 1.47 2.00 1.25 — 2.30 0.5 0.70 0.71 0.42 Amine* 0.6 0.75 0.6 0.75 0.37 0.60 0.37 0.6 0.37 0.37Perfume X^(e) 0.40 0.13 0.065 0.25 0.03 0.030 0.030  0.065 0.03 0.03Phase 0.21 0.25 0.21 0.21 0.14 — —  0.14 — — Stabilizing Polymer ^(f)Suds — — — — — — — 0.1 — — Suppressor ^(g) Calcium 0.15 0.176 0.15 0.150.30 0.176 — 0.1-0.15 — — Chloride DTPA ^(h) 0.017 0.017 0.017 0.0170.007 0.007 0.20 — 0.002 0.002 Preservative 5 5 5 5 5 5 — 250 ^(j)   5 5(ppm) ^(i,j) Antifoam^(k) 0.015 0.018 0.015 0.015 0.015 0.015 — — 0.0150.015 Dye (ppm) 40 40 40 40 40 40 11 30-300 30 30 Ammonium 0.100 0.1180.100 0.100 0.115 0.115 — — — — Chloride HCl 0.012 0.014 0.012 0.0120.028 0.028 0.016  0.025 0.011 0.011 Structurant^(l) 0.01 0.01 0.01 0.010.01 0.01 0.01  0.01 0.01 0.01 Additional 0.8 0.7 0.9 0.5 1.2 0.5 1.10.6 1.0 0.9 Neat Perfume Deionized † † † † † † † † † † Water ^(a)N,N-di(tallowoyloxyethyl)-N,N-dimethylammonium chloride. ^(b) Methylbis(tallow amidoethyl)2-hydroxyethyl ammonium methyl sulfate. ^(c)Reaction product of Fatty acid with Methyldiethanolamine in a molarratio 1.5:1, quaternized with Methylchloride, resulting in a 1:1 molarmixture of N,N-bis(stearoyl-oxy-ethyl) N,N-dimethyl ammonium chlorideand N-(stearoyl-oxy-ethyl) N,-hydroxyethyl N,N dimethyl ammoniumchloride. ^(d) Cationic high amylose maize starch available fromNational Starch under the trade name CATO ®. ^(e)Perfume comprising oneor more Table 1 PRMs. ^(f) Copolymer of ethylene oxide and terephthalatehaving the formula described in U.S. Pat. No. 5,574,179 at col. 15,lines 1-5, wherein each X is methyl, each n is 40, u is 4, each R1 isessentially 1,4-phenylene moieties, each R2 is essentially ethylene,1,2-propylene moieties, or mixtures thereof. ^(g) SE39 from Wacker ^(h)Diethylenetriaminepentaacetic acid. ^(i) KATHON ® CG available from Rohmand Haas Co. “PPM” is “parts per million.” ^(j) Gluteraldehyde^(k)Silicone antifoam agent available from Dow Corning Corp. under thetrade name DC2310. ^(l)Hydrophobically-modified ethoxylated urethaneavailable from Rohm and Haas under the tradename Aculan 44. *One or morematerials comprising an amine moiety as disclosed in the presentspecification. † balance

Example 6 Dry Laundry Formulations

% w/w granular laundry detergent composition Component A B C D E F GBrightener 0.1 0.1 0.1 0.2 0.1 0.2 0.1 Soap 0.6 0.6 0.6 0.6 0.6 0.6 0.6Ethylenediamine disuccinic acid 0.1 0.1 0.1 0.1 0.1 0.1 0.1Acrylate/maleate copolymer 1.5 1.5 1.5 1.5 1.5 1.5 1.5 Hydroxyethanedi(methylene 0.4 0.4 0.4 0.4 0.4 0.4 0.4 phosphonic acid) Mono-C₁₂₋₁₄alkyl, di-methyl, 0.5 0.5 0.5 0.5 0.5 0.5 0.5 mono-hydroyethylquaternary ammonium chloride Linear alkyl benzene 0.1 0.1 0.2 0.1 0.10.2 0.1 Linear alkyl benzene sulphonate 10.3 10.1 19.9 14.7 10.3 17 10.5Magnesium sulphate 0.4 0.4 0.4 0.4 0.4 0.4 0.4 Sodium carbonate 19.519.2 10.1 18.5 29.9 10.1 16.8 Sodium sulphate 29.6 29.8 38.8 15.1 24.419.7 19.1 Sodium Chloride 0.1 0.1 0.1 0.1 0.1 0.1 0.1 Zeolite 9.6 9.48.1 18 10 13.2 17.3 Photobleach particle 0.1 0.1 0.2 0.1 0.2 0.1 0.2Blue and red carbonate speckles 1.8 1.8 1.8 1.8 1.8 1.8 1.8 EthoxylatedAlcohol AE7 1 1 1 1 1 1 1 Tetraacetyl ethylene diamine 0.9 0.9 0.9 0.90.9 0.9 0.9 agglomerate (92 wt % active) Citric acid 1.4 1.4 1.4 1.4 1.41.4 1.4 PDMS/clay agglomerates (9.5% 10.5 10.3 5 15 5.1 7.3 10.2 wt %active PDMS) Polyethylene oxide 0.2 0.2 0.2 0.2 0.2 0.2 0.2 Enzymes e.g.Protease (84 mg/g 0.2 0.3 0.2 0.1 0.2 0.1 0.2 active), Amylase (22 mg/gactive) Suds suppressor agglomerate 0.2 0.2 0.2 0.2 0.2 0.2 0.2 (12.4 wt% active) Sodium percarbonate (having 7.2 7.1 4.9 5.4 6.9 19.3 13.1 from12% to 15% active AvOx) Additional Neat Perfume** 0.5 0.5 0.5 0.5 0.50.5 0.5 Amine* 0.1 0.5 0.0 0.01 0.02 0.00 0.07 Perfume Delivery SystemAs 0.05 0.0 0.1 0.0 0.2 0.4 0.0 Disclosed In The Present SpecificationIncluding Examples 2-4 Perfume comprising one or more 0.3 0.4 0.01 0.020.04 0.1 0.1 PRMs from Table 1 Water 1.4 1.4 1.4 1.4 1.4 1.4 1.4 Misc0.1 0.1 0.1 0.1 0.1 0.1 0.1 Total Parts 100 100 100 100 100 100 100 *Oneor more materials comprising an amine moiety as disclosed in the presentspecification. **Optional

Example 7 Liquid Laundry Formulations (HDLs)

Ingredient HDL 1 HDL 2 HDL3 HDL4 HDL 5 HDL 6 Alkyl Ether Sulphate 0.000.50 12.0 12.0 6.0 7.0 Dodecyl Benzene 8.0 8.0 1.0 1.0 2.0 3.0 SulphonicAcid Ethoxylated Alcohol 8.0 6.0 5.0 7.0 5.0 3.0 Citric Acid 5.0 3.0 3.05.0 2.0 3.0 Fatty Acid 3.0 5.0 5.0 3.0 6.0 5.0 Ethoxysulfated 1.9 1.21.5 2.0 1.0 1.0 hexamethylene diamine quaternized Diethylene triaminepenta 0.3 0.2 0.2 0.3 0.1 0.2 methylene phosphonic acid Enzymes 1.200.80 0 1.2 0 0.8 Brightener (disulphonated 0.14 0.09 0 0.14 0.01 0.09diamino stilbene based FWA) Cationic hydroxyethyl 0 0 0.10 0 0.200 0.30cellulose Poly(acrylamide-co- 0 0 0 0.50 0.10 0 diallyldimethylammoniumchloride) Hydrogenated Castor Oil 0.50 0.44 0.2 0.2 0.3 0.3 StructurantBoric acid 2.4 1.5 1.0 2.4 1.0 1.5 Ethanol 0.50 1.0 2.0 2.0 1.0 1.0 1,2propanediol 2.0 3.0 1.0 1.0 0.01 0.01 Glutaraldehyde 0 0 19 ppm 0 13 ppm0 Diethyleneglycol (DEG) 1.6 0 0 0 0 0 2,3-Methyl-1,3- 1.0 1.0 0 0 0 0propanediol (M pdiol) Mono Ethanol Amine 1.0 0.5 0 0 0 0 NaOH SufficientTo pH 8 pH 8 pH 8 pH 8 pH 8 pH 8 Provide Formulation pH of: SodiumCumene 2.00 0 0 0 0 0 Sulphonate (NaCS) Silicone (PDMS) emulsion 0.0030.003 0.003 0.003 0.003 0.003 Additional Neat Perfume** 0.7 0.5 0.8 0.80.6 0.6 Amine* 0.01 0.10 0.0 0.10 0.20 0.05 Perfume comprising one or0.02 0.15 0.0 0.2 0.3 0.1 more PRMs from Table 1 Perfume Delivery System0.2 0.02 0.4 0.0 0.0 0.0 As Disclosed In The Present SpecificationIncluding Examples 2-4 Water Balance Balance Balance Balance BalanceBalance *One or more materials comprising an amine moiety as disclosedin the present specification. **Optional.

Example 8 Shampoo Formulations

Ingredient Ammonium Laureth Sulfate (AE₃S) 6.00 Ammonium Lauryl Sulfate(ALS) 10.00  Laureth-4 Alcohol 0.90 Trihydroxystearin ⁽⁷⁾ 0.10 Perfumecomprising one or more 0.60 PRMs from Table 1 Sodium Chloride 0.40Citric Acid 0.04 Sodium Citrate 0.40 Sodium Benzoate 0.25 EthyleneDiamine Tetra Acetic Acid 0.10 Dimethicone ^((9, 10, 11))  1.00 ⁽⁹⁾Water and Minors (QS to 100%) Balance

Example 9 Fine Fragrance Formulations

Ingredient 1 2 3 Cyclic oligosaccharide 0 5 10 Ethanol 90 75 80 Perfumecomprising one or more 10 20 10 PRMs from Table 1

The dimensions and values disclosed herein are not to be understood asbeing strictly limited to the exact numerical values recited. Instead,unless otherwise specified, each such dimension is intended to mean boththe recited value and a functionally equivalent range surrounding thatvalue. For example, a dimension disclosed as “40 mm” is intended to mean“about 40 mm”.

All documents cited in the Detailed Description of the Invention are, inrelevant part, incorporated herein by reference; the citation of anydocument is not to be construed as an admission that it is prior artwith respect to the present invention. To the extent that any meaning ordefinition of a term in this document conflicts with any meaning ordefinition of the same term in a document incorporated by reference, themeaning or definition assigned to that term in this document shallgovern.

While particular embodiments of the present invention have beenillustrated and described, it would be obvious to those skilled in theart that various other changes and modifications can be made withoutdeparting from the spirit and scope of the invention. It is thereforeintended to cover in the appended claims all such changes andmodifications that are within the scope of this invention.

What is claimed is:
 1. A consumer product comprising an adjunctingredient and, based on total consumer product weight, from about0.0001% to about 25% of one or more perfume raw material selected from:4-(2,4-dimethyl-cyclohex-3-enylidene)-butan-2-one and all stereoisomersof 4-(2,4-dimethyl-cyclohex-3-enylidene)-butan-2-one; and one or moreoptional perfume raw materials selected from:4-isopropyl-1,5-dimethyl-2-oxa-bicyclol[2.2.2]octane;4-(1,2-dimethyl-propyl)-1-methyl-2-oxa-bicyclol[2.2.2]octane; 2-(3-methyl-butyl)-3-vinyl-cyclopentanone;2,5,5-trimethyl-2-propyl-[1,3]dioxane;1,2,4-trimethyl-bicyclol[2.2.1]lheptane-2-carboxylic acid methyl ester;8-ethoxy-2,6-dimethyl-nona-2,6-diene;2,2,3a,7-tetramethyl-octahydro-benzofuran;4-cyclopropylmethoxymethyl-5-methyl-cyclohexene; cyclopropanecarboxylicacid 1-methyl-hexyl ester;3-isopropenyl-6-methyl-2-propenyl-tetrahydro-pyran; acetic acid3-isopropyl-1,2-dimethyl-cyclopentyl ester;1-(2,4,6-trimethyl-cyclohex-3-enyl)-propan-1-one;2-(hex-3-enyl)-5-methyl-tetrahydro-furan;3-sec-Butyl-1,5-dimethyl-2-oxa-bicyclo[2.2.2]octane;1-(6-Isopropyl-2-methyl-cyclohex-3-enyl)-ethanone;1-(6-Isopropyl-4-methyl-cyclohex-3-enyl)-ethanone;4-(3-Methoxy-l-methyl-propyl)-1-methyl-cyclohexene;3-(1,1-Dimethoxy-ethyl)-1,1-dimethyl-cyclohexane;2,4-Dimethyl-2-(4-methyl-pent-3-nyl)-[1,3]dioxolane;3a-isopropyl-2,6-dimethyl-octahydro-benzofuran; and all stereoisomers ofsaid one or more optional perfume raw materials.
 2. A consumer productaccording to claim 1, said consumer product being a cleaning and/ortreatment composition.
 3. A consumer product according to claim 1, saidconsumer product being a fabric and/or hard surface cleaning and/ortreatment composition.
 4. A consumer product according to claim 1, saidconsumer product being a detergent.
 5. A consumer product according toclaim 1, said consumer product being a highly compacted consumerproduct.
 6. A consumer product according to claim 5, said consumerproduct being a highly compacted detergent.
 7. A perfume delivery systemcomprising from about 001% to about 50% of one or more perfume rawmaterial selected from:4-(2,4-dimethyl-cyclohex-3-enylidene)-butan-2-one and stereoisomers of4-(2,4-dimethyl-cyclohex-3-enylidene)-butan-2-one; and one or moreoptional perfume raw materials selected from: 4-isopropyl-1,5-dimethyl-2-oxa- bicyclo[2.2.2]octane;4-(1,2-dimethyl-propyl)-1-methyl-2-oxa-bicyclo[2.2.2]octane; 2-(3-methyl-butyl)-3-vinyl-cyclopentanone;2,5,5-trimethyl-2-propyl-[1,3]dioxane;1,2,4-trimethyl-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester;8-ethoxy-2,6-dimethyl-nona-2,6-diene;2,2,3a,7-tetramethyl-octahydro-benzofuran;4-cyclopropylmethoxymethyl-5-methyl-cyclohexene; cyclopropanecarboxylicacid 1-methyl-hexyl ester;3-isopropenyl-6-methyl-2-propenyl-tetrahydro-pyran; acetic acid3-isopropyl-1,2-dimethyl-cyclopentyl ester;1-(2,4,6-trimethyl-cyclohex-3-enyl)-propan-1-one;2-(hex-3-enyl)-5-methyl-tetrahydro-furan;3-sec-Butyl-1,5-dimethyl-2-oxa-bicyclo[2.2.2]octane;1-(6-Isopropyl-2-methyl-cyclohex-3 -enyl)-ethanone;1-(6-Isopropyl-4-methyl-cyclohex-3-enyl)-ethanone;4-(3-Methoxy-1-methyl-propyl)-1-methyl-cyclohexene;3-(1,1-Dimethoxy-ethyl)-1,1-dimethyl-cyclohexane;2,4-Dimethyl-2-(4-methyl-pent-3-nyl)-[1,3]dioxolane;3a-isopropyl-2,6-dimethyl-octahydro-benzofuran; and all stereoisomers ofsaid one or more optional perfume raw materials, wherein said perfumedelivery system is selected from a polymer assisted delivery system; amolecule-assisted delivery system; a fiber-assisted delivery system; anamine assisted delivery system; a cyclodextrin delivery system; a starchencapsulated accord; an inorganic carrier delivery system; or apro-perfume.
 8. A perfume delivery system according to claim 7, saidperfume delivery system being a nanocapsule or a microcapsule.
 9. Aperfume delivery system according to claim 8, said perfume deliverysystem being a starch encapsulated accord.
 10. A perfume delivery systemaccording to claim 7, said perfume delivery system being a cyclodextrindelivery system.
 11. A perfume delivery system according to claim 7,said perfume delivery system being a polymer assisted delivery matrixsystem.
 12. A perfume delivery system according to claim 7, said perfumedelivery system being an amine assisted delivery system.
 13. A perfumedelivery system according to claim 7, said perfume delivery system beinga pro-perfume amine reaction product.
 14. The perfume delivery systemaccording to claim 13, said perfume delivery system comprising one ormore perfume raw material selected from Table 1 Nos. 2, 5, 6 and 21.